O-[(1S)-1-[(2S,3R)-3-methyloxiran-2-yl]but-3-enyl] imidazole-1-carbothioate | 157922-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: O-[(1S)-1-[(2S,3R)-3-methyloxiran-2-yl]but-3-enyl] imidazole-1-carbothioate
• CAS: 157922-52-6
• 化学式: C₁₁H₁₄N₂O₂S
• 分子量: 238.31
• InChiKey: AJHGLIPREMFBGF-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-[(1S)-1-[(2S,3R)-3-methyloxiran-2-yl]but-3-enyl] imidazole-1-carbothioate 在 盐酸 、 二甲基硫 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 生成 (3aR,4R,6S,7aS)-6-methoxy-4-methyl-4,6,7,7a-tetrahydro-3aH-[1,3]oxathiolo[4,5-c]pyran-2-one
  参考文献：
  名称：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1

  摘要：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.

  DOI：

  10.1016/s0040-4039(00)73285-0
• 作为产物：
  描述：

  (4R,5R,6R)-5,6-epoxyhept-1-en-4-ol 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 、 对硝基苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 O-[(1S)-1-[(2S,3R)-3-methyloxiran-2-yl]but-3-enyl] imidazole-1-carbothioate
  参考文献：
  名称：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1

  摘要：

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.

  DOI：

  10.1016/s0040-4039(00)73285-0

文献信息

• A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1
  作者：William R. Roush、Darin Gustin

  DOI：10.1016/s0040-4039(00)73285-0

  日期：1994.7

  A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.